5136 W Winona Street — Chicago, IL 60630
Active Under Contract
Chicago, IL 60630

5136 W Winona Street

$689,000
3 beds · 2 baths · 1,653 sqft
Listed at $689,000 11 days on market $8,116/yr taxes
01About this home

Welcome to 5136 Winona St, an exceptional Chicago bungalow that seamlessly blends timeless character with thoughtful modern updates, ideally positioned on a quiet, tree-lined street in the heart of Jefferson Park. Situated on an extra-wide lot, this residence offers an expansive and highly functional layout across three beautifully finished levels. The main level showcases sun-drenched living and dining spaces, designed for both everyday living and effortless entertaining. The updated kitchen is appointed with stainless steel appliances and flows seamlessly into the heart of the home. Two bedrooms and a well-appointed full bath complete this level, along with a charming enclosed three-season room-perfectly suited for a private office, wellness space, or creative retreat. Upstairs, the second level offers a tranquil escape with an additional bedroom and dedicated office or dormer space, ideal for today's flexible lifestyle. The fully finished basement, renovated in 2021 and featuring rare 10-foot ceilings, delivers an impressive extension of living space. This level includes a generous family room, oversized bedroom with a walk-in closet, and a second full bathroom. Outdoor living is equally compelling, with a fully fenced yard, private patio, expansive side yard, two-car garage, and additional parking pad-an uncommon convenience in the city. Located just moments away from the Jefferson Park Blue Line, Metra, and I-90/94. This home is a commuter's dream. You are within walking distance to local favorites, top-rated schools, and the sprawling greenery of Gladstone and Jefferson Parks. Don't miss out! This home offers the perfect blend of suburban comfort in the city!

02Inside the home
03By the numbers
$689,000
List price
1,653
Square feet
3
Bedrooms
2 full
Bathrooms
1914
Year built
Lot size
2
Garage spaces
$8,116
Annual taxes
Detached Single
Style
11
Days on market
04Features
Heating
Natural GasForced Air
Cooling
Central Air
Parking
Garage OwnedDetachedOwnedGarage
Construction
Frame
Sewer
Public Sewer
05Neighborhood
This home EElementary school
E Elementary school
Beaubien Elementary School
Chicago, IL
📍0.2 mi🚗1 min🚶4 min
  • Bust Outs 0.2 mi
  • Rabbit’s Bar and Grill 0.2 mi
  • Subway 0.4 mi
  • Jefferson Park Grill 0.4 mi
  • Kawayan 0.4 mi
  • Excelsior Garden 0.4 mi
  • Mariano's Fresh Market 0.4 mi
  • Eden's Food and Liquors 0.4 mi
  • Marathon 0.4 mi
  • Mobil Mart 0.4 mi
  • 7-Eleven 0.4 mi
  • ANG Convenience Store 0.4 mi
  • Roberts Square Park 0.2 mi
  • Forest Glen Park 0.2 mi
  • Grace Zwiefka Thuis Park 0.5 mi
  • Jefferson Memorial Park 0.6 mi
  • Ashmore Park 0.6 mi
  • Frank Wilson Park 0.7 mi
  • Dunkin' 0.4 mi
  • Dunkin' 0.5 mi
  • Weston's Coffee & Tap Co. 0.5 mi
  • Mr. B's Caribbean Grill 0.5 mi
  • Starbucks 0.5 mi
  • Red Ribbon 0.5 mi
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

May 14, 2026
Listed for saleThis listing
Keller Williams Premiere Properties
$689,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

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08See it for yourself

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09Similar homes
Listed by Keller Williams Premiere Properties · Maria Montes De Oca
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12638398
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